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Chlorine-Substituted N-Heteroacene Analogues Acting as Organic Semiconductors for Solution-Processed n-type Organic
Bo Yang1, Zilong Wang2, Tengfei He3
1Key Laboratory for Organic Electronics and Information Displays, Institute of Advanced Materials (IAM), Nanjing University of Posts & Telecommunications, 9 Wenyuan Road, Nanjing, 210023, P.R. China.
Abstract:
High performance solution processable n-type organic semiconductor is an essential element to realize low-cost, all organic and flexible composite logic circuits. In the design of n-type semiconducting materials, tuning the LUMO level of compounds is a key point. As a strong electron withdrawing unit, the introduction of chlorine atom into the chemical structure can increase the electron affinity of the material and reduce the LUMO energy level. Here, a series chlorine substituted N-heteroacene analogues of 6,7,8,9-tetrachloro-4,11-bis(4-((2-ethylhexyl)oxy)phenyl)-[1,2,5]thiadiazolo[3,4-b]phenazine (O4Cl), 6,7,8,9-tetrachloro-4,11-bis(4-((2-ethylhexyl)thio)phenyl)-[1,2,5]thiadiazolo[3,4-b]phenazine (S4Cl), 1,2,3,4,8,9,10,11-octachloro-6,13-bis(4-((2-ethylhexyl)oxy)phenyl)quinoxalino[2,3-b]phenazine (8Cl) and 12Cl have been synthesized and characterized. Solution-processed organic field-effect transistors (OFETs) based on these four compounds exhibit good electron mobilities of 0.04 cm2 V-1 s-1 , 0.01 cm2 V-1 s-1 , 2×10-3 cm2 V-1 s-1 and 3×10-3 cm2 V-1 s-1 , respectively, under ambient conditions. The results suggest that these chlorine substituted π-conjugated N-heteroacene analogues are promising n-type semiconductors in OFET applications.
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